A Convenient and General Method for the Synthesis of Indole‐2,3‐dicarboxylates and 2‐Arylindole‐3‐carboxylates

作者: Iliyas Ali Sayyed , Karolin Alex , Annegret Tillack , Nicolle Schwarz , Dirk Michalik

DOI: 10.1002/EJOC.200700310

关键词: DominoOrganic chemistryChemistryIndole testHydroaminationFischerindoleGeneral methodAcetylene

摘要: A transition-metal-free, simple and efficient one-pot method for the synthesis of indole-2,3-dicarboxylates 2-arylindole-3-carboxylates is described. The corresponding products are obtained by a domino hydroamination/Fischerindole cyclization in good-to-excellent yields from easily available 1-alkyl-1-phenylhydrazines acetylene carboxylates.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

参考文章(57)
Richard J. Sundberg, The chemistry of indoles ,(1970)
Vivek Khedkar, Annegret Tillack, Christoph Benisch, Johann-Peter Melder, Matthias Beller, Base-catalyzed hydroamination of ethylene with diethylamine Journal of Molecular Catalysis A-chemical. ,vol. 241, pp. 175- 183 ,(2005) , 10.1016/J.MOLCATA.2005.06.068
Adam M. Johns, Masaru Utsunomiya, Christopher D. Incarvito, John F. Hartwig, A highly active palladium catalyst for intermolecular hydroamination. Factors that control reactivity and additions of functionalized anilines to dienes and vinylarenes. Journal of the American Chemical Society. ,vol. 128, pp. 1828- 1839 ,(2006) , 10.1021/JA056003Z
DSC Black, N Kumar, LCH Wong, Synthesis of 4,6-Dimethoxyindoles Australian Journal of Chemistry. ,vol. 39, pp. 15- 20 ,(1986) , 10.1071/CH9860015
Changsheng Cao, Yanhui Shi, Aaron L. Odom, Intermolecular alkyne hydroaminations involving 1,1-disubstituted hydrazines. Organic Letters. ,vol. 4, pp. 2853- 2856 ,(2002) , 10.1021/OL0201052
H. Schwesinger, Antje Dalski, D. Sicker, H. Wilde, G. Mann, Synthese substituierter 2-Nitrophenylhydrazone von 2-Oxodicarbonsäureestern und Untersuchung ihres Tautomerie- und Absorptionsverhaltens† Journal Fur Praktische Chemie-chemiker-zeitung. ,vol. 334, pp. 257- 264 ,(1992) , 10.1002/PRAC.19923340311
Masao. Nakazaki, Koji. Yamamoto, Direct synthesis of indole by the Fischer indole synthesis Journal of Organic Chemistry. ,vol. 41, pp. 1877- 1877 ,(1976) , 10.1021/JO00872A045
J. Duflos, G. Queguiner, Cycloaddition reactions of an o-quinoid 10-.pi.-electron system, 2H-pyrrolo[3,4-c]pyridine Journal of Organic Chemistry. ,vol. 12, pp. 1195- 1198 ,(1981) , 10.1021/JO00319A030